This quaint island -- a happy medium between well-developed Cape Cod and isolated Nantucket -- offers pristine beaches, boutique shops, and a taste of the region's maritime past.
Edgartown and Oak Bluffs are picturesque New England seaside towns, but still have shopping and entertainment options, like wine bars, ice cream parlors, and elegant boutiques. On the western side of the island, towns like Chilmark and Menemsha provide a more remote experience.
Although restaurants are often on the pricey side, they're typically worth the extra green. Competition in the foodie world is fierce on this island, as the restaurants here have some of the finest service and cuisine on the east coast.
Visitors eager for nightlife might want to look for hotels in Oak Bluffs and Edgartown, as alcohol is less of a focus elsewhere (several towns even choose to be dry). That being said, visitors hoping to fully escape from crazy city life might prefer the western areas of Chilmark and Aquinnah, the most peaceful options. You'll find the most options within the busier parts of the island -- Edgartown, Vineyard Haven, and Oak Bluffs -- but a few decent alternatives can be found in the isolated western areas.